(Part 6 in an 8-part series of topics to contemplate in major gift fundraising.  This series of blogs is designed for boards, CEOs and advancement staff.)   


So far in this blog series, The Journey from Fear to Bold Asking, I’ve talked about many of the components that are important to a successful fundraising ask:  the power of connecting with people in meaningful ways; leading with passion;  being willing and able to tell your story; developing and using good active listening (questioning) skills; and building a well-honed team to support the journey.   

You may want to take a few minutes to brush up on these past blogs, and the toolkits that I’ve included, before diving into this one. 

The final three blogs of this series will focus on Starting the Conversation; Boldly, Making the Ask; and finally Saying Thank You, Abundantly! 

So, let’s get started with the conversation, because that’s where it all begins.   

Throughout my career as a consultant, and even before as a Chief Development Officer at leading U.S. medical schools and hospitals, I’ve had brilliant leaders, even leaders in their fields, tell me they weren’t comfortable with starting a conversation with a potential donor.  So, if you find yourself in this group, don’t despair!  You’re in great company.   

I don’t think the discomfort these highly educated people felt came from the lack of something important and meaningful to share.  Quite the contrary!  Most often it came from the fear and total dislike of having to engage in what they perceived as “small talk” with people, especially if they were completely not well known to them.  I don’t blame them!  There are probably very few of us who truly enjoy standing around in a crowded ballroom making “small talk” with people we’ve just met.   

Fortunately, that’s not what starting a genuine prospective donor conversation is all about!  Before you invite a new donor or prospect to truly make a transformative difference in your organization and in their own lives, you must authentically understand and appreciate the person and their life circumstances.   

If you’ve not read my blog, The Secrets of Creating Meaningful Bonds, I suggest you take another break and read that blog.  I think it would be helpful to brush up on the material in this blog.  In particular, pay attention to the role human connections and meaningful experiences play in philanthropy. 

So, before we go on, I need to be completely honest and say, if you are not the kind of person who genuinely cares about people and  truly enjoys interacting with them, you’re going to have some challenges with donor conversations and the eventual ask.  

So, take a minute and do a self- evaluation. If this describes you, if you struggle with interpersonal skills, you may be able to be a successful fundraiser, but you will likely benefit from a really strong partner! And, your partner will need to fully understand his or her role with you. We all benefit from strong teams and partners in philanthropic work.  But, if you do not enjoy interacting with people, a trusted partner is absolutely essential!

I also want to clarify what I mean by “Starting the Conversation”.  This is not the conversation where the “ask” or the invitation to participate in a cause, campaign or institutional priority occurs.  Nope, this is the conversation that importantly must come long before any gift conversation.  It’s about establishing connection and a meaningful relationship. And, it's about listening and learning! 

One of the things I’ve frequently seen in my career is the lack of purposeful donor or new partner conversations.  This is especially true of organizations that are in campaigns with large, looming goals (of course, that’s just about all, since everything is relative) or managing an annual fund drive that determines whether or not they “make the institutional budget".  We do ourselves and our philanthropy partners a great disservice when time is not made for meaningful donor conversations.   Below is my Toolkit for "Starting the Conversation",  including everything from creating the right environment to making sure the conversation continues. 

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Collaterals can be great leave behinds or follow up tools.  Resist using them, however, as a crutch in your first conversation.  Rather, you want to draw out your prospect.  Collaterals can help provide a follow up conversation. 


1. The Place:  The place where this first conversation, and hopefully many more, occur is important.  Where the conversation occurs  and who else, if anyone, is involved is highly dependent on the prospective donor(s). If the prospect or donor is a high capacity, major donor prospect, the first conversation may occur with the President or Executive Director, or with the Chief Development Officer, alone.  In some cases, the conversation may also include a board member, or maybe a development officer.  This is where good judgement really comes into play.  This is an opportunity to simply get to know one another.  It is important that the place convey this message.   
It is important that the conversation occur in a place that is welcoming and non-threatening.  In some cases, the prestige of meeting with the President alone in his or her office over a cup of coffee may be appealing.  Whatever place is chosen, make it easy for the prospective donor. That may mean going to the prospect’s office or home or a convenient coffee shop or quiet restaurant.
Do not try to have this conversation at a fundraising event!  (Read that sentence again!) Your annual gala or golf outing may be a great place to say instead, “I’d love to get together for a cup of coffee.  May I call you next week to see if we can arrange a convenient time?” 

2. The Invitation:  Just as in the case of “the ask”, the person doing the inviting needs to be the hardest person to say no to.   Please don’t use text, unless requested, to arrange this conversation!  I even prefer that email is used only after a phone conversation, if at all possible!  The invitation should be personal.  So, the President, the board member of the development officer, whomever is hosting the meeting, should call first.  In some cases, a letter may be more appropriate.  Again, the approach depends on the prospect, so use your best judgement. But, whatever mode is used, it must be personal.  Remember, a lot will be learned in that first call. Then a follow up call or email from an assistant to coordinate a meeting time is fine. 

Most importantly, the invitation lays the groundwork for the conversation.  Here are some suggestions to use when you extend the invitation.  

  • Always begin by offering gratitude, perhaps gratitude for a past gift, gratitude for attending an event, or simply gratitude for visiting the organization.  Here’s an example that could apply to the president or development officer: 

    “I recently learned of your wonderful donation to our organization.  We are so grateful for your support.  I’m interested in getting better acquainted and learning more about your perspectives on our work.  Would you be willing to join me for coffee/lunch at a time that works well in your schedule?”   If possible, set up the appointment during that conversation rather than leaving it to an assistant later on. 

    Or, here’s another scenario that would apply to a board member: 

    “Sarah, thank you for joining us at last week’s Children’s Hospital gala.  I’ve served on the board for many years and it meant a lot to me to share the evening with you.  I’d really like for the hospital president to get better acquainted with you.  She’s making an enormous difference in the health of the children of our community and I think your perspectives could be very valuable to her and what we’re building together.  Would you be willing to sit down with us over lunch or coffee?  Perhaps you could give me a few dates that work for you, and I’ll get back to you by {Friday} with some dates.”  
  • In every case, not matter who is extending the invitation, it needs to always be clear that
    •  You are grateful for the prospect or donor’s interest.

    • You are truly interested in the prospect’s perspectives and thoughts. 

    • You genuinely have an interest in the person and a meaningful conversation that matters to both parties. 

  •  Make sure the next step and follow up is clear, with an agreed upon action and a date by which time that action will occur.  Do not leave anything to chance, and have a specific actionable timeline, for example: “If I don’t hear back from you by next week with a few dates, may my assistant, Ben, or I follow up with you in 10 days?”  And then, act on your agreement!  Letting time slip can be the kiss of death to this future conversation!  I find that follow through is a huge problem.  So make a commitment to following through on your commitments!
  • One other recommendation:  be gently and appropriately persistent! 

3. The Homework: The research conducted by the development office is crucial. Whether the meeting occurs with the President, a board member or the chief development officer, don’t skip this step! No matter who is conducting the meeting, it is important to come prepared to help guide the conversation and understand a little bit about the person you're meeting with. Oftentimes, your best information comes from someone who knows the person well.  I prefer a short briefing that includes the following: 

  • Name and spouse or partner’s name 
  • Birthdate  
  • Children 
  • Home and business addresses 
  • Contact info, phone and email 
  • Business title and description 
  • College and post graduate education 
  • Philanthropic interests and examples of giving 
  • Hobbies and interests, if known

Although spontaneity is important, I have found that having a little background is helpful to asking the right questions and find points of common interests.


4.  The Conversation: Make sure you are clear on your objectives for the conversation.  Your objectives will be guided by the depth and maturity of the relationship. 

Is this a new relationship or one that is being refreshed after some months or years?  If the conversation follows on the heels of a one-time donation to the annual fund that is very different from following up after a visit to your hospital or school or attendance at a gala.

Remember, at this point, the conversation is not about money; at least not about a gift!  It’s about establishing a connection and then a meaningful relationship. (Please, read that sentence one more time!)Hopefully, this conversation will allow you to get to know the cares, concerns and passions of your guest and to understand their perspectives on the work your organization brings to the community or the world!  

I suggest asking open-ended questions, and then to truly listen!  Below are a few examples to help get the ball rolling.  As I listen to my nearly four-year old grandson, I am reminded that the best questions almost always begin with “why” or "what": 

  • I am grateful you agreed to spend some time with me today.  I'd appreciate knowing more about you and your family and what influenced you to join me today.
  • I am interested in your history with our organization. Why did you get involved with us?  Why have you stayed involved with us?
  • Our good friend, Jane, told me about your interest in our organization.  I'd love to know more about what interests you in our work.
  • I'd like to share some of our plans that I think you'd be interested in, but tell me first about what is more important to you about what we do.
  • Are there others at our organization, on the board or staff, that you and your family are close to?
  • I'm hosting a small gathering soon at my home that will include several of our board members and staff.  If you are interested in joining us, we will reach out to make sure you receive an invitation.
  • I am creating a list of people that we hope share an interest in our work.  Would you be willing to help us think about others we should reach out to?

“It’s about establishing a connection and then a meaningful relationship. ”

5.  Continuing the Conversation:  Okay, so this is just the start!  Hopefully, you have found some common ground and discovered points that are worth continuing the conversation and most importantly, a future relationship. 

Again, remember, this conversation is not about asking for money.  Do not ask for a gift!  Don’t even bring it up…. Except possibly to say, “I’m not here today to ask you for a gift.”  This is about understanding the meaning that your organization brings to this prospective partner’s life and understanding his or her views of the world and your institution.  Do, however, ask for a second appointment!  Based on your conversation, perhaps there are others in the organization that are appropriate to introduce next.  Maybe there is an upcoming program that would appropriate, or perhaps a small dinner gathering of like-minded board members.  And, it is almost always appropriate to ask, “Are there others I should reach out to as we continue to connect with people in our community who have been touched by our mission?” 

Now that you’ve taken some of the most important steps, and hopefully your prospective partner has shown interest, the next blog will get into the actual ask….. even a bold ask that comes from a place of comfort and confidence!   

Onward and upward!